Skatole

Names

Preferred IUPAC name

3-Methyl-1H-indole

Other names

3-Methylindole
4-Methyl-2,3-benzopyrrole

Identifiers

CAS Number

83-34-1^Y

3D model (Jmol)

Interactive image
Interactive image

CHEBI:9171^Y

6480^Y

9W945B5H7R^Y

InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3^Y

Key: ZFRKQXVRDFCRJG-UHFFFAOYSA-N^Y
InChI=1/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3

Key: ZFRKQXVRDFCRJG-UHFFFAOYAZ

SMILES

C1=C2C(=CC=C1)C(=C[N]2C)C
c1cccc2c1c(cn2)C

Properties

Chemical formula

C₉H₉N

Molar mass

131.18 g·mol⁻¹

Appearance

White crystalline solid

Melting point

93 to 95 °C (199 to 203 °F; 366 to 368 K)

Boiling point

265 °C (509 °F; 538 K)

Solubility in water

Insoluble

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Skatole or 3-methylindole is a mildly toxic white crystalline organic compound belonging to the indole family. It occurs naturally in feces (it is produced from tryptophan in the mammalian digestive tract) and coal tar and has a strong fecal odor. In low concentrations, it has a flowery smell and is found in several flowers and essential oils, including those of orange blossoms, jasmine, and Ziziphus mauritiana. It is used as a fragrance and fixative in many perfumes and as an aroma compound. Its name is derived from the Greek root skato- meaning "dung". Skatole was discovered in 1877 by the German physician Ludwig Brieger (1849–1919). Skatole is also used by U.S. military in its non-lethal weaponry; specifically, malodorants.

Skatole can be found as a white crystalline or fine powder solid, and it browns upon aging. It is nitrogenous, and one of the rings is a pyrrole. It is soluble in alcohol and benzene, and it gives a violet color in potassium ferrocyanide (K₄Fe(CN)₆·3H₂O) and sulfuric acid (H₂S O₄). Skatole has a double ring system that displays aromaticity. It is continuous (all atoms in the ring are sp² hybridized), planar, and follows the 4n+2 rule because it has 10 π electrons. It can be synthesized through a Fischer indole synthesis, which was developed by Emil Fischer.

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